Cyclopentylamine → N-(5-Chloro-2,4-dimethoxy-phenyl)-2-(3-cyclopentylcarbamoylmethyl-2-oxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamide

HRID 472742Notes

Reaction equation

HRID 472742 reaction equation
[Cl:1][C:2]1[C:3]([O:29][CH3:30])=[CH:4][C:5]([O:27][CH3:28])=[C:6]([NH:8][C:9]([CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][N:14]([CH2:22][C:23](O)=[O:24])[C:13]2=[O:26])=[O:10])[CH:7]=1.CN(C(ON1N=N[C:41]2[CH:42]=[CH:43][CH:44]=[N:45][C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CCCC1>CS(C)=O>[Cl:1][C:2]1[C:3]([O:29][CH3:30])=[CH:4][C:5]([O:27][CH3:28])=[C:6]([NH:8][C:9](=[O:10])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][N:14]([CH2:22][C:23](=[O:24])[NH:45][CH:40]3[CH2:41][CH2:42][CH2:43][CH2:44]3)[C:13]2=[O:26])[CH:7]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59317691{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid

Product 1

HCID 59317677N-(5-Chloro-2,4-dimethoxy-phenyl)-2-(3-cyclopentylcarbamoylmethyl-2-oxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid (Example 5-1) (20 mg, 0.046 mmol) in DMSO (1 ml) is treated with a solution of HATU (19.3 mg, 0.05 mmol) in DMSO (2 ml). The reaction mixture is then treated with cyclopentylamine (4.12 mg, 0.048 mmol) and the reaction left to stand at RT overnight. The reactions are analysed by HPLC/LCMS and concentrated in vacuo. The residue is taken up in DCM and washed with 1M HCl The organic phase is washed with saturated NaHCO3 and concentrated in vacuo to give the title compound; [M+H]+ 501

Workup

  1. waitthe reaction left
  2. concentrationconcentrated in vacuo
  3. washwashed with 1M HCl The organic phase
  4. washis washed with saturated NaHCO3
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d08f9af85b174625986c9bd38fc82c06
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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